DE1543325A1 - Process for the preparation of o- (2-N-acyloxy-N-acylaminoacylamino) phenylaryl ketones - Google Patents
Process for the preparation of o- (2-N-acyloxy-N-acylaminoacylamino) phenylaryl ketonesInfo
- Publication number
- DE1543325A1 DE1543325A1 DE19641543325 DE1543325A DE1543325A1 DE 1543325 A1 DE1543325 A1 DE 1543325A1 DE 19641543325 DE19641543325 DE 19641543325 DE 1543325 A DE1543325 A DE 1543325A DE 1543325 A1 DE1543325 A1 DE 1543325A1
- Authority
- DE
- Germany
- Prior art keywords
- acylamino
- ketones
- acyloxy
- phenylaryl
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
70/ab
AHP-3030 (b)-G70 / from
AHP-3030 (b) -G
American Home Products Corporation, New YorkB N.Ye/üSA Verfahren zur Herstellung von o-(2-K-Acylo3cy-Ii-acylamino-American Home Products Corporation, New York B NY e / üSA Process for the production of o- (2-K-Acylo3cy-Ii-acylamino-
acylamino)-phenylary!ketonen„acylamino) phenylary! ketones "
sssssssssssssssxsssssscsssssssacscssssssts&iscssesssssssssssssssxsssssscsssssssacscssssssts & iscsse
Die vorliegende Erfindung betrifft ein Verfahren aur Herstellung von o- (2-N~Acyloxy~N->acylamino-acylamino) -phenylary!ketonen, The present invention relates to a process for the preparation of o- (2-N-acyloxy-N-> acylamino-acylamino) -phenylary! Ketones,
Das erfindungsgemäße Verfahren sur Herstellung von o-(2-N-Acyloxy~N-acylamino-acylamino)~phenylary!ketonen bestent darin, daß man ein entsprechendes o~(2-Hydroxyamino-acylamino)-phenylary!keton unter nicht-cyclisierenden Bedingungen acylierteThe process according to the invention for the preparation of o- (2-N-acyloxy-N-acylamino-acylamino) -phenyl aryl ketones the best thing is that a corresponding o ~ (2-hydroxyamino-acylamino) -phenylary! ketone is used under non-cyclizing conditions acylated
Als Beispiele für o~{2-Hydroxyamino-acylamino)°<phenylarylketone9 die Mach dem erfinclungsgemäßen Verfahren als Ausgangsmaterialien verwendet bzw,, von o-(2-N-Acy!oxy-N-acylamino-acylamino)-phenylary!ketonen» die erfindungsgemäß hergestellt werden, können Verbindungen der allgemeinen Formel I genannt werden: 9098A2/1717 % As examples of o ~ {2-hydroxyamino-acylamino) ° <phenylaryl ketones 9 the Mach the process according to the invention used as starting materials or of o- (2-N-Acy! Oxy-N-acylamino-acylamino) -phenylary! Ketones » which are prepared according to the invention, compounds of the general formula I can be named: 9098A2 / 1717 %
ι !„·...,i„r,.--r. :.λ ν;' α· ..·. ■■■■ ■ ■ ■-■ ■ ■ ···■-'-™.w ···'■■< "'·ι! "· ..., i" r , .-- r. : .λ ν; ' α · .. ·. ■■■■ ■ ■ ■ - ■ ■ ■ ··· ■ -'- ™ .w ··· '■■ <"' ·
ArAr
wobei der Ring A unsubstitniert oder durch einen oder mehrere, in die Reaktion nicht eingreifende Substituenten substituiert sein kann, s«B. durch ein oder zwei Wasserstoff atome, niedere Alkyl-, Chlor-, Brom-, Nitro-P Halogen-niedrigalky!gruppen, a.B. Erifluormethyl oder AlkyiaiOfonyl-, z.B· Methylaulfonyigruppen; R bedeutet Waoserstoff oder einen Alkylrest, BoBo niedffig-AXkyl oder niedrig-Aralkyli R1 und R2 bedeuten Wasserstoff oder eine oder swei Aikylgruppe»· ü«B. niedrig-Alkyl, Aralkyl, ί5·Β» niedrig^Aralkyl odsr Ai*y3.g5?uppsn5 R^ und R, bedeuten in den AiisgaiigsmateriaXien beide Vfesoex'stoff, bavr. in den Verfah3?ensx>rodukten beide Acylgimppen, j3eBo Acetyl; und Ar bedeutet einen Arylreat oder Heteroarylrest* s»Bo 1- oder 2-Naphthyl, vorsugöweise ^edocli einen monocyclischen Arylreet wie Phenyl, oder Phenyl substituiert durch eine oder mehrere j in die Rf?alcöion nicht eingreifende Gruppen wie Halogen» K0B0 Chlor oder Brom, nie&rig-Alkyl, niedrig-AXko3ye Halogen-niedrig-Aüsyl, v/ie a^B, iSrifluormethyl, oder Alkyl-, wie ss. B. Me thy !sulfonyl, einen 2- oder 3-furyl-; 2- oder 3-Thienyl- oder 2-, 3- oder 4-?yridylreat.where the ring A can be unsubstituted or substituted by one or more substituents which do not intervene in the reaction, s «B. atoms by one or two hydrogen, lower alkyl, chlorine, bromine, nitro P halogen niedrigalky groups, aB Erifluormethyl or AlkyiaiOfonyl- such Methylaulfonyigruppen ·!; R denotes hydrogen or an alkyl radical, BoBo low-AXkyl or lower-aralkyl R 1 and R 2 denote hydrogen or one or two alkyl groups "" B. lower-alkyl, aralkyl, 5 · Β »lower ^ aralkyl or odsr Ai * y3.g5? uppsn5 R ^ and R, both mean Vfesoex'stoff, bavr. In the process products both acyl gimps, j3 e B o acetyl; and Ar denotes an arylate or heteroaryl radical * s »B o 1- or 2-naphthyl, preferably a monocyclic aryl radical such as phenyl, or phenyl substituted by one or more groups which do not intervene in the Rf? alcoion such as halogen» K 0 B 0 chlorine or bromine, never & rig-alkyl, low-AXko3y e halogen-low-aüsyl, v / ie a ^ B, isrifluoromethyl, or alkyl, like ss. B. methyl sulfonyl, a 2- or 3-furyl; 2- or 3-thienyl- or 2-, 3- or 4-? Yridylreat.
9098A2/1717 '9098A2 / 1717 '
Der hler verwendete Ausdruck Alky!gruppe umfaßt Methyl- f Äthyl-, Propyl-, Isopropyl«, η-Butyl-, Isoamyl-j Alkenyl- und Alkinylgruppen wie Allyl, Methallyl, Äthlnyl, Propeuyl und Vinyl; und öycloalkylgruppen wie Cyclopropyl, Cyclobutyl und Cyclopentyl» Unter niedrig-Alkyl ist eine Alkylgruppe mit bis BU 6 Kohlenstoffatomen zu verstehen« Unter niedrig-Aralkyl ist ein Aralkylreot mit bis zu 9 Kohlenstoffatomen au verstehen, s.B. Benzyl oder Phenäthyl. Unter niedrig-Allcoxy ist eine Gruppe mit bis au 6 Kohlenstoff atomen zu verstehen.! The counter used expression alky group includes methyl f ethyl, propyl, isopropyl, "η-butyl, isoamyl j alkenyl and alkynyl groups such as allyl, methallyl, Äthlnyl, Propeuyl and vinyl; and cycloalkyl groups such as cyclopropyl, cyclobutyl and cyclopentyl "Lower-alkyl is to be understood as an alkyl group with up to 6 carbon atoms". Lower-aralkyl is understood to mean an aralkyl group with up to 9 carbon atoms, eg benzyl or phenethyl. Low-alkoxy is to be understood as meaning a group with up to 6 carbon atoms.
Insbesondere können einer oder beide Heute R1 und R2 Zwecke der Erläuterung Alky!gruppen sein, κ.B. Methyl, Äthyl, Propyl, Isopropyl, n«Butylr t-Butyl, Isoamyl und, wenn beide Gruppen derartige Roste «ind, können sie gleich oder verschieden oder miteinander verbunden sein unter Bildung eines KohlonvrasoerstoffringeH wie eines niedrig-Cycloalkylrestee wie Cyclopropyl, Cyclobutyl und Cyolopentyl, und ungesättigte Alkylgruppnn wie Vinyl, Äthinyl und IPropsnyl und sie könne». Arylreste darstellen, wie Phenyl oder einen Phenylrest, der mit Gruppen eubntituiert ist, die in die Reaktion nicht eingreif onf vfie Halogen, nicdrig-Alkyl und Hydroxyr iiwd sie können Arallcylreste bedeutenP wie Benayl oder Phenäthylf in denen die Pheny!gruppe ähnlich wie oben unoubetituiert oder substituiert sein kann.In particular, one or both of today's R 1 and R 2 can be alkyl groups for purposes of illustration, κ.B. Methyl, ethyl, propyl, isopropyl, n "butyl r t-butyl, isoamyl and, when both groups such gratings" ind, they may be connected the same or different or together to form a KohlonvrasoerstoffringeH such as a low-Cycloalkylrestee such as cyclopropyl, cyclobutyl, and Cyolopentyl, and unsaturated alkyl groups such as vinyl, ethynyl and IPropsnyl and they can ». Aryl radicals such as phenyl or a phenyl radical which is eubntituiert with groups in the reaction is not engaging on f vfie halogen, nicdrig alkyl and hydroxy r they iiwd can Arallcylreste mean P as Benayl or phenethyl f in which group the biphenyl similar can be unsubstituted or substituted as above.
B/.D 9098^2/ 1717B / .D 9098 ^ 2/1717
tit τtit τ
Die ο- (2-H-Acyloxy-Ii-acy lamino-acy!amino) -phenylarylketone werden geeigneterweise in Abwesenheit eines Cyclisierungsmittels durch Behandeln der entsprechenden o-(2-Hydroxyemino)-Verbindung mit einem Überschuß eines Aoylierungsmittels, wie Essigsäureanhydrid, Acetyl-chlorid, Keten, Isopropenyl-acetat oder einem anderen Ke-fcen-Ersseuger, Äthylchlorformiat, t-Butoxy-p-nitrophenyl-carbonat oder Carbotert.-butyloxyaf3idf hergestellt» Die Acylierung kann in Gegenwart oder Abwesenheit eines XÖsungsnittels erfolgen und unter mildem Erwärmen durchgeführt werden, wobei ein gege-* benenfalls verwendetes !lösungsmittel gegenüber dem Acylicrungsisittel inert sein muß. Wird kein Lösungsmittel verwendet, kann der Reaktionsverlauf durch das Verschwinden des o-(2-*Hydro3cyamino-acetatiiclo)-Reaktionspartners verfolgt werden. Im allgemeinen läuft die Reaktion schnell ab, um jedoch eine gute Ausbeute sicherzustellen, läßt man das Reaktionsgemisch mehrere Stunden unter schwachem Erwärmen stehen, obgleich die temperatur, bei weloher die Reaktion abläuft, nicht so hoch sein sollte, daß Zersetzung des gewünschten Endprodukte stattfindet»The ο- (2-H-acyloxy-Ii-acy lamino-acy! Amino) -phenylaryl ketones are suitably prepared in the absence of a cyclizing agent by treating the corresponding o- (2-hydroxyemino) compound with an excess of an aoylating agent such as acetic anhydride, acetyl -chloride, ketene, isopropenyl acetate or another ketene acid, ethyl chloroformate, t-butoxy-p-nitrophenyl carbonate or carbotert.-butyloxyaf3id f produced »The acylation can take place in the presence or absence of a solvent and with mild warming be carried out, whereby any solvent used must be inert to the acylic agent. If no solvent is used, the course of the reaction can be followed by the disappearance of the o- (2- * Hydro3cyamino-acetatiiclo) reaction partner. In general, the reaction proceeds quickly, but in order to ensure a good yield, the reaction mixture is left to stand for several hours under gentle heating, although the temperature at which the reaction takes place should not be so high that decomposition of the desired end product takes place »
Die nach dein erfindungsgemäßen Verfahren hergestellten o-(2-H-Aoylos3r-ir-^acylamino-acylamino)-phenylarylketone können unter sauren Oyclisierungsbedingungen einen Ringsohluß unterThose produced by the process of the invention o- (2-H-Aoylos3r-ir- ^ acylamino-acylamino) -phenylarylketone can a ring base under acidic cyclization conditions
9098A2/1717 '9098A2 / 1717 '
Bildung von 1 „Formation of 1 "
oxyden erleiden, die g6wünschtenfalls? wenn die Reste R1 und R2 der ]?o:2ael I beide Wasserstoff bedeuten, au 3-Acyloxy»1,3-dihydro-5-a3ryl-2H-1t4-bengodiaiSöpin«2-o]u.Qn acyliert und dann gegebenenfalls au den entsprechenden ^«Hydroaqr-'i g 3-diliydro-5-aryl«-2H»1,4-benaodiazepiii~2-onen hydrolysiert werden können» Diese cyclioierten Verbindungen sseigen paycholeptische Wirkungen bei Säugetieren, wie durch Standardtestmethoden gesseigt wurde· Sie sind für medizinische Zwecke wertvoll,, da aie eine Wirkung, als anticonvuleive, sedative oder muekelrel&xie^&nde Mittel aufweisen,, Einige davon haben eine Aktivität als Dämpfungsmittel' für das zentrale Nervensystem»suffer oxides, if so desired ? if the radicals R 1 and R 2 of the]? o: 2ael I are both hydrogen, acylated au 3-acyloxy »1,3-dihydro-5-a3ryl-2H-1 t 4-bengodiaiSöpin« 2-o] u.Qn and then optionally the corresponding au ^ «Hydroaqr-'i g of 3-diliydro-5-aryl" -2H "1,4-benaodiazepiii ~ 2-ones can be hydrolyzed" These compounds cyclioierten sseigen paycholeptische effects in mammals, such as by standard test methods gesseigt became · They are valuable for medical purposes ,, as they have an effect as anticonvuleive, sedative or muekelrel & xie ^ & nde agents ,, Some of them have an activity as depressants' for the central nervous system »
Die Cyclisierung der örfindungsgeinäßen Produkte ist im Starampatent . βββ βο» (Patentanmeldung A 46 104 IVd/i2qu) beschrieben«The cyclization of the products according to the invention is in the Staram patent. βββ βο »(patent application A 46 104 IVd / i2qu) described«
Wenn gewünscht wird, ein derartiges 1,3-Dihydro-5-aryl-2H-1,4~bensodiasepin~S-on au synthetiffiereiR,,, muß das eils Zwi-0chenpi?odulct gebildete o«{2-Er-Acyloxy~H~acylaraino-acylaBiino)~ phenylary!keton au«3 dem Reäktionegemisch nicht isoliert werden, in welchem es gebildet wird, und dieses kann beispielsweise mit starker Säure angesäuert werden, wobei die entsprechend© cyolisierte Verbindung gebildet wird, und dies ißt vorteilhaft ssur Verringerung der gahl der Verfahrensstufen, welcheIf desired, such a 1,3-dihydro-5-aryl-2H-1,4-bensodiasepin-S-one au synthetiffiereiR ,,, the speed between the two must be modulated formed o «{2-Er-acyloxy ~ H ~ acylaraino-acylaBiino) ~ phenylary! ketone cannot be isolated from the reaction mixture, in which it is formed, and this can for example acidified with strong acid, with the corresponding © cyolized compound is formed, and this is beneficial in reducing the number of process steps which
909842/1717'909842/1717 '
15A332515A3325
die Isolierung eines Zwischenprodukts srfordernο Beim einfachen Verdünnen des Reaktionsgeiaisches mit Wasser wird das Zwischenprodukt erhalten, und dieses kann in einem wäßrigen oder netebaren nichtwäßrigen organischen Lösungsmittel gelöst und dann mit dem Cyolisierungsmittel behandelt werden»the isolation of an intermediate product is required by simply diluting the reaction gel with water Obtained intermediate product, and this can be dissolved in an aqueous or wettable non-aqueous organic solvent and then treated with the cyolizing agent »
Die für das erfindungegemäfie Verfahren als Auegangeinaterialien verwendeten o-(2~Hydro3^7aioiino*-acylaiaino)«'phenylarylketone können durch tfmsetssung von HyaroxyD^min mit einem o-(2-subdtituierten Acy3.acij.uo)-phenylaryllceton hergestellt werden, wobei der 2-Substituent einem nucleophilen Ersatz durch Hydroxylamin üntervforfen wird. Diesen Verfahren ist in der fatenteckrift o o o π „ „ „ (Patentanmeldung, die von der gleichen Anmelderin am selben Sage unter dem Internen Aktenzeichen AHP-303Q (a)-6 eingereicht wurde) beschrieben.The o- (2 ~ Hydro3 ^ 7aioiino * -acylaiaino) «'phenylaryl ketones used as exit materials for the process according to the invention can be prepared by mixing hyaroxyD ^ min with an o- (2-substituted acij.uo) -phenylaryl acetone, whereby the 2-substituent is subjected to nucleophilic replacement by hydroxylamine. This method is described in the fatenteckrift ooo π """(patent application filed by the same applicant on the same day under the internal file number AHP-303Q (a) -6).
Bas folgende Beispiel erläutert die Sr£indung:The following example explains the induction:
Ein Gemisch von 5-Chlor-2-(21-hydroxyamiB.o-'acetaraido)-bemsophenon in Esßigsäureanhydrid wird 10 Minuten auf aam Dampfbad erhitzt, bis der gesamte Feststoff gelöst ißt,, und dann gekühlt. Der gebildete Niederschlag 2-(2'-N-Acetoxyff-acetylamino-acetamido )~5~chlorbensiophenont SchuielsspunktA mixture of 5-chloro-2- (2 1 -hydroxyamiB.o-'acetaraido) -bemsophenone in acetic anhydride is heated on a steam bath for 10 minutes until all of the solid is dissolved and then cooled. The formed precipitate of 2- (2'-N-Acetoxyff-acetylamino-acetamido) ~ 5 ~ t chlorbensiophenon Schuielsspunkt
909842/1717 '909842/1717 '
ι 51 bis 155°ö, wird gesammelt»ι 51 to 155 ° ö, is collected »
Analyse; C19H1725 Analysis; C 19 H 1725
berechnet* 0 58,70 H 4,41 N 7,41 Cl 9,12 $ calculated * 0 58.70 H 4.41 N 7.41 Cl $ 9.12 gefunden: C 58,68 H 4,42 K 7,11 Cl 9,1 #β Found: C 58.68 H 4.42 K 7.11 Cl 9.1 # β
Diese Verbindung zeigte bei pharmakologlßchen Unterisuohungen sedative Aktivität.This compound has shown in pharmacological disorders sedative activity.
Venn die obige Terhindung in Äthylalkohol ouspenäiert wire1., welchem ein Überschuß an Salsssäure zugegeben wurde, unü dae Oenieoh einige Hinuten gekocht und dann abkühlen gelassen wird, kufe «in Hiedereohlag von 7-0hlor-1,5-*dihydro-5-phonyl~2H-1,4Mbeni!odiaBepin-2-on-4-*O3cyd, Sohmelzpunki 238 bis ° gesammelt werden;Venn the above Terhindung in ethyl alcohol ouspenäiert wire 1., Which was added an excess of Salsssäure, is cooked New York Convention dae Oenieoh some Hinuten and then allowed to cool, Kufe, "in Hiedereohlag of 7-0hlor-1,5-dihydro-5-phonyl * ~ 2H-1.4 M beni! OdiaBepin-2-on-4- * O3cyd, Sohmelzpunki 238 to ° can be collected;
BAD CrJGINALBATHROOM CrJGINAL
9098^2/1717 "9098 ^ 2/1717 "
Claims (2)
Applications Claiming Priority (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28396663A | 1963-05-29 | 1963-05-29 | |
| US28396763A | 1963-05-29 | 1963-05-29 | |
| US28396663 | 1963-05-29 | ||
| US28396763 | 1963-05-29 | ||
| US30187363A | 1963-08-13 | 1963-08-13 | |
| US30177163A | 1963-08-13 | 1963-08-13 | |
| US30187363 | 1963-08-13 | ||
| US30177163 | 1963-08-13 | ||
| US32766763A | 1963-12-03 | 1963-12-03 | |
| US32766763 | 1963-12-03 | ||
| US36577364A | 1964-05-07 | 1964-05-07 | |
| US36577364 | 1964-05-07 | ||
| DEA0053985 | 1964-05-21 | ||
| US402374A US3257382A (en) | 1963-05-29 | 1964-09-11 | Preparation of 1, 3-dihydro-5-phenyl-2h-1, 4-benzodiazepin-2-one 4-oxide compounds |
| US644900A US3401200A (en) | 1963-05-29 | 1967-06-09 | Intermediates for the preparation of 1, 3-dihydro-5-aryl-2h-1, 4-benzodiazepin-2-ones 4-oxides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1543325A1 true DE1543325A1 (en) | 1969-10-16 |
| DE1543325B2 DE1543325B2 (en) | 1975-09-04 |
| DE1543325C3 DE1543325C3 (en) | 1976-05-26 |
Family
ID=
Also Published As
| Publication number | Publication date |
|---|---|
| US3401200A (en) | 1968-09-10 |
| DE1793731B2 (en) | 1977-07-07 |
| DE1793259B2 (en) | 1975-08-21 |
| DE1793731A1 (en) | 1973-07-05 |
| DE1795231A1 (en) | 1972-04-13 |
| GB1021381A (en) | 1966-03-02 |
| DE1295563B (en) | 1969-05-22 |
| CH468974A (en) | 1969-02-28 |
| DE1795231B2 (en) | 1977-11-17 |
| CH471136A (en) | 1969-04-15 |
| GB1021382A (en) | 1966-03-02 |
| US3257382A (en) | 1966-06-21 |
| DE1300114B (en) | 1969-07-31 |
| CH468973A (en) | 1969-02-28 |
| DE1795231C3 (en) | 1978-07-13 |
| DE1793259A1 (en) | 1972-02-03 |
| DE1543325B2 (en) | 1975-09-04 |
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